Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate → 5-(4-Fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid

HRID 1043053Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:19])[C:10]([C:14]([O:16]CC)=[O:15])=[CH:11][NH:12][CH:13]=2)=[CH:4][CH:3]=1>[OH-].[Na+]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:19])[C:10]([C:14]([OH:16])=[O:15])=[CH:11][NH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

The above ester (1.0 g, 3.8 mmol) was dissolved in 2N NaOH (20 mL) and heated to 65° C. for 2 h. The resulting clear mixture was cooled to ambient temperature and the solids were filtered off. The filtrate was then acidified with 1N HCl to pH=1 and the resulting yellow precipitate was collected as the desired product (0.73 g, 82%). 1H NMR (DMSO-d6) δ 13.52 (br s, 1H), 8.86 (s, 1H), 8.51 (s, 1H), 7.99-7.96 (m, 2H), 7.55-7.51 (m, 2H); MS (ESI+) m/z 234 (M+H)+.

Workup

temperatureThe resulting clear mixture was cooled to ambient temperature
filtrationthe solids were filtered off
customthe resulting yellow precipitate was collected as the desired product (0.73 g, 82%)

Sources & evidence

ORD record: ord-895d8b044a5d44c4a92301f81c2cf8c6
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08558000B2

Reaction notes

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